Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Expedient green-chemistry approaches for one-pot synthesis of two series of novel 1,5-benzodiazepines via domino reactions

Abstract

Unique green-chemistry approaches have been developed for the one-pot synthesis of two series of novel 1,5-benzodiazepines 4 and 5. The CeCl3-KI promoted two-component domino reaction of 1,2-phenylenediamines with 1,3-acetonedicarboxylate in ethanol afforded novel 1,5-benzodiazepin-2-ones 4. An expedient approach to 1,5-benzodiazepines 5 has also been developed via three-component domino reactions using 1,2-phenylenediamines, 1,3-acetonedicarboxylate and aldehydes in the presence of a catalytic amount of magnetic nanoparticles (γ-Fe2O3@SiO2/CeCl3) in ethanol at ambient temperature. During the above one-pot synthesis process, one new seven-membered nitrogen heterocycle (diazepin) and four new bonds (one C–C, two C–N and one C=C) were constructed by the nucleophilic addition, elimination reaction (dehydration etc.), hydride transfer and cyclization process. Structures of all 48 products were fully confirmed by spectroscopic techniques and by single-crystal X-ray analysis of 5db. Moreover, plausible synthesis reaction mechanisms of two series of novel 1,5-benzodiazepines 4 and 5 have been proposed. The methods have advantages such as operational simplicity, mild reaction conditions, short reaction time, easy recovery and reusability of the catalyst, high yields of products, and non-toxic EtOH as the solvent.

Back to tab navigation

Supplementary files

Article information


Submitted
22 Dec 2019
Accepted
17 May 2020
First published
18 May 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

Expedient green-chemistry approaches for one-pot synthesis of two series of novel 1,5-benzodiazepines via domino reactions

L. Wang and H. wu, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ06332C

Social activity

Search articles by author

Spotlight

Advertisements